Reactions of trifluoro- and hexafluoroacetylacetones with thiobenzoylhydrazine |
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Authors: | V V Alekseyev V V Pakal’nis I V Zerova S I Yakimovich |
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Institution: | 1. S. M. Kirov Military Medical Academy, 6 ul. Akad. Lebedeva, 194044, Saint Petersburg, Russian Federation 2. Saint Petersburg State University, 26 Universitetsky prosp., 198504, Saint Petersburg, Russian Federation
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Abstract: | The reaction of thiobenzoylhydrazine with trifluoroacetylacetone leads to the product of condensation at the CH3C=O bond with the 5-hydroxy-2-pyrazoline structure. The tautomeric transition to the 2,3-dihydro-1,3,4-thiadiazole isomer occurs in solution. This isomer undergoes the cleavage to 2-methyl-5-phenyl-1,3,4-thiadiazole and trifluoroacetone. The reaction of thiobenzoylhydrazine with hexafluoroacetylacetone affords one of diastereomers of 3,5-dihydroxy-3,5-bis(trifluoromethyl)pyrazolidin-1-yl](phenyl)thioketone, which at equilibrium is transformed in solution into the second diastereomer of the 3,5-dihydroxypyrazolidine form followed by the elimination of water elements and formation of a tautomeric 5-hydroxy-2-pyrazoline-2,3-dihydro-1,3,4-thiadiazole mixture. |
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